trans-4-(trans-4-Butylcyclohexyl)cyclohexanol → Trifluoroacetic acid 4-(4-butylcyclohexyl)cyclohexyl ester

HRID 2119274Notes

Reaction equation

HRID 2119274 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3](C1C2N=NNC=2C=CC=1)=[O:4].[CH2:16]([CH:20]1[CH2:25][CH2:24][CH:23]([CH:26]2[CH2:31][CH2:30][CH:29]([OH:32])[CH2:28][CH2:27]2)[CH2:22][CH2:21]1)[CH2:17][CH2:18][CH3:19]>C1COCC1>[CH2:16]([CH:20]1[CH2:25][CH2:24][CH:23]([CH:26]2[CH2:27][CH2:28][CH:29]([O:32][C:3](=[O:4])[C:2]([F:15])([F:14])[F:1])[CH2:30][CH2:31]2)[CH2:22][CH2:21]1)[CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 23440384trans-4-(trans-4-Butylcyclohexyl)cyclohexanolHCID 178519451HCID 178519451, compound

Product 1

HCID 20615164Trifluoroacetic acid 4-(4-butylcyclohexyl)cyclohexyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trifluoroacetylbenzotriazole in an amount of 7.5 g (35 mmol) was dissolved in 75 ml of THF, 4.6 g (19 mmol) of 4-(4-butyl-cyclohexyl)cyclohexanol was added thereto, they were refluxed for 1 hour, and then the solvent was distilled off. After the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=5/1), the solvent was distilled off, the residue was subjected twice to recrystallization by using heptane to give 1.5 g (4.5 mmol) of trifluoroacetic acid 4-(4-butylcyclohexyl)cyclohexyl ester. Yield of this compound based on 4-(4-butylcyclohexyl)cyclohexanol was 24%.

Workup

  1. temperaturethey were refluxed for 1 hour
  2. distillationthe solvent was distilled off
  3. customAfter the residue was purified by column chromatography on silica gel (eluent: heptane/ethyl acetate=5/1)
  4. distillationthe solvent was distilled off
  5. customthe residue was subjected twice to recrystallization

Sources & evidence

ORD record
ord-152d0f179b18419f81b9c16d741713ce
Source dataset
uspto-grants-2004_02
Patent number
US06685995B1

Reaction notes

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